Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate; methanol / 3 h / 20 °C / Cooling with ice
1.2: 16 h / 20 °C
2.1: potassium carbonate; N-benzyl-N,N,N-triethylammonium chloride / 1,4-dioxane / 4 h / 90 °C
3.1: sodium hydride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere
3.2: 17 h / 20 °C / Cooling with ice
4.1: hydrogen bromide; acetic acid; phenol / 12 h / 75 °C / sealed tube; microwave irradiation
5.1: dmap / dichloromethane / 1 h
6.1: hydrazine hydrate / iron(III) chloride hexahydrate / methanol / 5 h / Reflux
6.2: 7 h / Reflux
7.1: trifluoroacetic acid / 2,2,2-trifluoroethanol / 0.33 h / 100 °C / microwave irradiation
8.1: water; lithium hydroxide monohydrate / tetrahydrofuran / 18 h
8.2: pH 3
9.1: N-ethyl-N,N-diisopropylamine; ammonium carbonate; HATU / N,N-dimethyl-formamide / 18 h / 20 °C
With
methanol; sodium tetrahydroborate; hydrazine hydrate; lithium hydroxide monohydrate; N-benzyl-N,N,N-triethylammonium chloride; water; hydrogen bromide; ammonium carbonate; sodium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; phenol;
dmap; iron(III) chloride hexahydrate;
In
tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; 2,2,2-trifluoroethanol; N,N-dimethyl-formamide;